(Di­methyl­phosphor­yl)methanaminium iodide–(di­methyl­phosphor­yl)methan­amine (1/1)

Reiss, G.J.

doi:10.1107/S1600536813019004

organic compounds

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ISSN: 2056-9890

Volume 69| Part 8| August 2013| Pages o1253-o1254

doi:10.1107/S1600536813019004

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(Dimethylphosphoryl)methanaminium iodide–(dimethylphosphoryl)methanamine (1/1)

Guido J. Reiss ^a ^*

^aInstitut für Anorganische Chemie und Strukturchemie, Lehrstuhl II: Material- und Strukturforschung, Heinrich-Heine-Universität Düsseldorf, Universitätsstrasse 1, D-40225 Düsseldorf, Germany
^*Correspondence e-mail: reissg@hhu.de

(Received 7 July 2013; accepted 9 July 2013; online 13 July 2013)

The asymmetric unit of the title structure, C₃H₁₁NOP⁺·I⁻·C₃H₁₀NOP, consists of one (dimethylphosphoryl)methanamine (dpma) molecule, one (dimethylphosphoryl)methanaminium (dpmaH) ion and one iodide counter-anion. In the crystal, medium–strong to weak N—H⋯O and N—H⋯N hydrogen bonds connect dpmaH cations and dpma molecules into strands along [001]. The iodide counter-anions form only very weak hydrogen bonds. The crystal used for the diffraction study was found to be an inversion twin with a ratio of 0.83 (2):0.17 (2). The title structure is isotypic to that of dpmaH[ClO₄]·dpma [Buhl et al. (2013 ). Crystals 3, 350–362].

Related literature

For transition metal complexes of the dpma ligand, see: Dodoff et al. (1990 ); Borisov et al. (1994 ); Trendafilova et al. (1997 ); Kochel (2009 ). For transition metal complexes of the cationic dpmaH ligand, see: Reiss (2013a ,b ). For dpmaH⁺ salts, see: Reiss & Jörgens (2012 ); Buhl et al. (2013); Lambertz et al. (2013 ). For the term tecton, see: Brunet et al. (1997 ). For the graph-set analysis method, see: Grell et al. (2002 ).

Experimental

Crystal data

C₃H₁₁NOP⁺·I⁻·C₃H₁₀NOP
M_r = 342.09
Orthorhombic, P c a 2₁
a = 17.7791 (3) Å
b = 11.1766 (2) Å
c = 6.91805 (12) Å
V = 1374.69 (4) Å³
Z = 4
Mo Kα radiation
μ = 2.54 mm⁻¹
T = 100 K
0.36 × 0.19 × 0.10 mm

Data collection

Oxford Diffraction Xcalibur Eos diffractometer
Absorption correction: analytical [CrysAlis PRO (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ), based on expressions derived by Clark & Reid (1995 )] T_min = 0.538, T_max = 0.808
10904 measured reflections
3062 independent reflections
2972 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.016
wR(F²) = 0.033
S = 1.05
3062 reflections
145 parameters
6 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.28 e Å⁻³
Absolute structure: Refined as an inversion twin.
Flack parameter: 0.173 (17)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H11⋯N2ⁱ	0.86 (3)	1.95 (3)	2.805 (4)	173 (3)
N1—H12⋯O1ⁱⁱ	0.86 (3)	1.96 (3)	2.824 (3)	177 (4)
N1—H13⋯O2	0.91 (3)	1.81 (3)	2.716 (4)	172 (4)
N2—H21⋯O1	0.82 (3)	2.17 (3)	2.965 (4)	163 (4)
N2—H22⋯I1	0.83 (3)	3.21 (3)	3.948 (3)	150 (4)
Symmetry codes: (i) x, y, z-1; (ii) $[-x+{\script{1\over 2}}, y, z-{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2011); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536813019004/zl2559sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813019004/zl2559Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813019004/zl2559Isup3.cml

checkCIF report

Comment top

(Dimethylphosphoryl)methanamine (dpma) is a promising bidentate ligand for the coordination of various transition metals (Dodoff et al., 1990; Borisov et al. 1994; Trendafilova et al., 1997; Kochel 2009). The corresponding N-protonated dpmaH cation is also known to form transition metal complexes (Reiss, 2013a, 2013b). For simple dpmaH salts it has been demonstrated that this tecton (for the term tecton see: Brunet et al., 1997) shows a distinct tendency to form one-dimensional polymers by hydrogen bonded head to tail connections of adjacent cations (Reiss & Jörgens, 2012; Lambertz et al. 2013, Buhl et al. 2013). This contribution is part of our ongoing interest in the construction of new hydrogen bonded network architectures using phosphoryl containing tectons.

As illustrated in Figure 1, the asymmetric unit of the title structure consists of one dpmaH cation, one dpma molecule, and one iodide anion in the non-centrosymmetric space group Pca2₁. Bond lengths and angles within the dpmaH cation and in the neutral dpma molecule are in the expected ranges (Buhl et al. 2013). The dpmaH cation and the dpma molecule are each connected head to tail via one strong and one moderate N–H···O hydrogen bond constructing a ten-membered ring (second level graph-set descriptor: R²₂(10); Figure 1 (red numbers)). Furthermore, these primary cyclic units are connected to adjacent units by N–H···N and N–H···O hydrogen bonds (Figure 2). These connections form one-dimensional strands running along [001]. The iodide counter anions form only very weak classical and non–classical hydrogen bonds, if at all. The hydrogen bonding motif of the backbone of the afore mentioned strands is represented by the second level graph-set descriptor C²₂(7) (Figure 2, red numbers). The connections of the dpmaH ^. dpma cyclic units with adjacent ones produce one more simple ring-motif, which can be described as a third level graph-set descriptor: R³₄(11) (Figure 2, green numbers). To visualize the basic principles of the construction a constructor graph is shown in Fig. 3 (Grell et al. 2002). The title structure is isotypic to the structure of dpmaH[ClO₄] ^. dpma (Buhl et al. 2013). However, there are differences in detail due to the nature of the iodide counter anion. For dpmaHI.dpma a 6% smaller volume of the unit cell has been determined. In both structures the counter anions are positioned in the vicinity of the amino group of the dpma molecule. The replacement of perchlorate by the significantly weaker hydrogen bonded iodide counter anion leads to a measurable strengthening of the hydrogen bond donating property of the amino group within the strands. The crystal which was used for the diffraction study was found to be an inversion twin with a ratio of 0.83 (2):0.17 (2).

Related literature top

For transition metal complexes of the dpma ligand, see: Dodoff et al. (1990); Borisov et al. (1994); Trendafilova et al. (1997); Kochel (2009). For transition metal complexes of the cationic dpmaH ligand, see: Reiss (2013a,b). For dpmaH⁺ salts, see: Reiss & Jörgens (2012); Buhl et al. (2013); Lambertz et al. (2013). For the term tecton, see: Brunet et al. (1997). For the graph-set analysis method, see: Grell et al. (2002).

Experimental top

In a typical experiment 0.5 g dpma was dissolved in 3 ml hydroiodic acid. The solution was slowly heated to dryness. The residual solid (dpmaHI) and an equimolar amount of dpma were dissolved im 5 ml methanol. Slow evaporation of this solution at room temperature yielded colorless crystals of the title compound.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2011); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The asymmetric unit of the title structure is shown with displacement ellipsoids drawn at the 70% probability level. Blue broken lines indicate hydrogen bonds. The red number marks the ring size of the second level R²₂(10) graph-set descriptor for this connection of the dpmaH cation with the dpma molecule.
	Fig. 2. The primary units are further connected via hydrogen bonds to form strands running along [001].
	Fig. 3. Constructor graph (Grell et al. 2002) of that part of the title structure shown in figure 2 (black dots: dpma, gray dots: dpmaH, arrows: crystallographic dependency is coded by the colours).

(Dimethylphosphoryl)methanaminium iodide–(dimethylphosphoryl)methanamine (1/1) top

Crystal data top

C₃H₁₁NOP⁺·I⁻·C₃H₁₀NOP	D_x = 1.653 Mg m⁻³
M_r = 342.09	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pca2₁	Cell parameters from 8874 reflections
a = 17.7791 (3) Å	θ = 2.9–29.4°
b = 11.1766 (2) Å	µ = 2.54 mm⁻¹
c = 6.91805 (12) Å	T = 100 K
V = 1374.69 (4) Å³	Block, colorless
Z = 4	0.36 × 0.19 × 0.10 mm
F(000) = 680

Data collection top

Oxford Diffraction Xcalibur Eos diffractometer	3062 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2972 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
Detector resolution: 16.2711 pixels mm^-1	θ_max = 27.5°, θ_min = 2.9°
ω scans	h = −21→22
Absorption correction: analytical [CrysAlis PRO (Oxford Diffraction, 2009), based on expressions derived by Clark & Reid (1995)]	k = −14→11
T_min = 0.538, T_max = 0.808	l = −8→8
10904 measured reflections

Refinement top

Refinement on F²	Hydrogen site location: difference Fourier map
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.016	w = 1/[σ²(F_o²) + (0.011P)² + 0.370P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.033	(Δ/σ)_max = 0.003
S = 1.05	Δρ_max = 0.32 e Å⁻³
3062 reflections	Δρ_min = −0.28 e Å⁻³
145 parameters	Extinction correction: SHELXL2013 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
6 restraints	Extinction coefficient: 0.00115 (12)
Primary atom site location: structure-invariant direct methods	Absolute structure: Refined as an inversion twin.
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.173 (17)

Crystal data top

C₃H₁₁NOP⁺·I⁻·C₃H₁₀NOP	V = 1374.69 (4) Å³
M_r = 342.09	Z = 4
Orthorhombic, Pca2₁	Mo Kα radiation
a = 17.7791 (3) Å	µ = 2.54 mm⁻¹
b = 11.1766 (2) Å	T = 100 K
c = 6.91805 (12) Å	0.36 × 0.19 × 0.10 mm

Data collection top

Oxford Diffraction Xcalibur Eos diffractometer	3062 independent reflections
Absorption correction: analytical [CrysAlis PRO (Oxford Diffraction, 2009), based on expressions derived by Clark & Reid (1995)]	2972 reflections with I > 2σ(I)
T_min = 0.538, T_max = 0.808	R_int = 0.023
10904 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.016	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.033	Δρ_max = 0.32 e Å⁻³
S = 1.05	Δρ_min = −0.28 e Å⁻³
3062 reflections	Absolute structure: Refined as an inversion twin.
145 parameters	Absolute structure parameter: 0.173 (17)
6 restraints

Special details top

Experimental. CrysAlisPro, Version 1.171.34.44, (Oxford Diffraction, 2009). Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by Clark & Reid (1995).

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refined as a 2-component inversion twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
I1	0.57385 (2)	0.73704 (2)	0.75007 (5)	0.01322 (6)
P1	0.34627 (4)	0.54054 (8)	0.66655 (12)	0.00984 (17)
O1	0.31186 (10)	0.62671 (19)	0.8072 (3)	0.0116 (5)
N1	0.33299 (15)	0.7173 (3)	0.3886 (4)	0.0110 (6)
H11	0.3537 (18)	0.748 (3)	0.288 (5)	0.025 (11)*
H12	0.2881 (17)	0.693 (4)	0.364 (5)	0.033 (12)*
H13	0.331 (2)	0.775 (3)	0.481 (6)	0.041 (13)*
C1	0.28010 (15)	0.4322 (3)	0.5842 (4)	0.0125 (7)
H1A	0.2643	0.3833	0.6909	0.019*
H1B	0.3031	0.3827	0.4874	0.019*
H1C	0.2372	0.4721	0.5299	0.019*
C2	0.42584 (14)	0.4612 (2)	0.7564 (8)	0.0164 (6)
H2A	0.4647	0.5170	0.7904	0.025*
H2B	0.4442	0.4077	0.6586	0.025*
H2C	0.4115	0.4161	0.8687	0.025*
C3	0.38262 (16)	0.6192 (3)	0.4555 (5)	0.0124 (7)
H3A	0.4316	0.6521	0.4865	0.015*
H3B	0.3892	0.5624	0.3509	0.015*
P2	0.35541 (4)	0.99276 (7)	0.78259 (13)	0.01040 (17)
O2	0.32571 (12)	0.9051 (2)	0.6371 (3)	0.0154 (5)
N2	0.38890 (15)	0.8119 (3)	1.0417 (4)	0.0120 (6)
H21	0.370 (2)	0.771 (3)	0.957 (5)	0.016 (10)*
H22	0.4349 (17)	0.809 (4)	1.022 (6)	0.033 (12)*
C4	0.44922 (15)	1.0407 (3)	0.7318 (6)	0.0170 (7)
H4A	0.4819	0.9723	0.7271	0.026*
H4B	0.4659	1.0942	0.8315	0.026*
H4C	0.4503	1.0811	0.6094	0.026*
C5	0.30034 (16)	1.1262 (3)	0.7964 (5)	0.0179 (8)
H5A	0.3036	1.1687	0.6761	0.027*
H5B	0.3190	1.1760	0.8989	0.027*
H5C	0.2488	1.1058	0.8217	0.027*
C6	0.35496 (16)	0.9310 (3)	1.0246 (4)	0.0119 (6)
H6A	0.3817	0.9854	1.1095	0.014*
H6B	0.3033	0.9267	1.0695	0.014*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I1	0.01355 (9)	0.01279 (10)	0.01334 (9)	0.00093 (6)	0.00029 (13)	0.00089 (17)
P1	0.0106 (4)	0.0092 (4)	0.0096 (4)	0.0003 (3)	0.0001 (3)	0.0014 (3)
O1	0.0137 (10)	0.0098 (12)	0.0112 (11)	−0.0002 (8)	0.0022 (8)	−0.0009 (8)
N1	0.0123 (14)	0.0099 (16)	0.0108 (13)	−0.0017 (11)	0.0011 (11)	0.0004 (12)
C1	0.0153 (15)	0.0105 (18)	0.0116 (15)	−0.0020 (12)	−0.0005 (13)	0.0001 (13)
C2	0.0149 (13)	0.0170 (15)	0.0172 (14)	0.0023 (11)	−0.0012 (17)	0.000 (3)
C3	0.0117 (15)	0.0118 (19)	0.0137 (15)	0.0010 (12)	0.0023 (13)	0.0011 (14)
P2	0.0105 (3)	0.0099 (4)	0.0108 (4)	0.0014 (3)	−0.0018 (3)	−0.0004 (3)
O2	0.0182 (11)	0.0133 (13)	0.0146 (12)	0.0035 (9)	−0.0032 (9)	−0.0035 (10)
N2	0.0126 (14)	0.0109 (16)	0.0125 (13)	−0.0015 (11)	−0.0009 (11)	0.0000 (13)
C4	0.0162 (14)	0.0208 (17)	0.0141 (19)	−0.0016 (11)	0.0015 (16)	0.0050 (19)
C5	0.0218 (15)	0.0124 (17)	0.020 (2)	0.0065 (12)	−0.0059 (13)	−0.0033 (13)
C6	0.0113 (15)	0.0113 (18)	0.0130 (15)	−0.0014 (12)	0.0006 (12)	0.0012 (13)

Geometric parameters (Å, º) top

P1—O1	1.500 (2)	P2—O2	1.501 (2)
P1—C2	1.782 (3)	P2—C4	1.787 (3)
P1—C1	1.782 (3)	P2—C5	1.787 (3)
P1—C3	1.823 (3)	P2—C6	1.811 (3)
N1—C3	1.481 (4)	N2—C6	1.467 (4)
N1—H11	0.86 (3)	N2—H21	0.82 (3)
N1—H12	0.86 (3)	N2—H22	0.83 (3)
N1—H13	0.91 (3)	C4—H4A	0.9600
C1—H1A	0.9600	C4—H4B	0.9600
C1—H1B	0.9600	C4—H4C	0.9600
C1—H1C	0.9600	C5—H5A	0.9600
C2—H2A	0.9600	C5—H5B	0.9600
C2—H2B	0.9600	C5—H5C	0.9600
C2—H2C	0.9600	C6—H6A	0.9700
C3—H3A	0.9700	C6—H6B	0.9700
C3—H3B	0.9700

O1—P1—C2	114.65 (19)	H3A—C3—H3B	107.7
O1—P1—C1	112.00 (13)	O2—P2—C4	113.09 (16)
C2—P1—C1	107.30 (15)	O2—P2—C5	112.85 (13)
O1—P1—C3	110.77 (14)	C4—P2—C5	105.77 (15)
C2—P1—C3	103.78 (18)	O2—P2—C6	111.70 (14)
C1—P1—C3	107.81 (15)	C4—P2—C6	107.47 (17)
C3—N1—H11	107 (2)	C5—P2—C6	105.44 (15)
C3—N1—H12	112 (3)	C6—N2—H21	106 (3)
H11—N1—H12	111 (4)	C6—N2—H22	115 (3)
C3—N1—H13	109 (3)	H21—N2—H22	106 (4)
H11—N1—H13	108 (3)	P2—C4—H4A	109.5
H12—N1—H13	109 (4)	P2—C4—H4B	109.5
P1—C1—H1A	109.5	H4A—C4—H4B	109.5
P1—C1—H1B	109.5	P2—C4—H4C	109.5
H1A—C1—H1B	109.5	H4A—C4—H4C	109.5
P1—C1—H1C	109.5	H4B—C4—H4C	109.5
H1A—C1—H1C	109.5	P2—C5—H5A	109.5
H1B—C1—H1C	109.5	P2—C5—H5B	109.5
P1—C2—H2A	109.5	H5A—C5—H5B	109.5
P1—C2—H2B	109.5	P2—C5—H5C	109.5
H2A—C2—H2B	109.5	H5A—C5—H5C	109.5
P1—C2—H2C	109.5	H5B—C5—H5C	109.5
H2A—C2—H2C	109.5	N2—C6—P2	114.7 (2)
H2B—C2—H2C	109.5	N2—C6—H6A	108.6
N1—C3—P1	113.3 (2)	P2—C6—H6A	108.6
N1—C3—H3A	108.9	N2—C6—H6B	108.6
P1—C3—H3A	108.9	P2—C6—H6B	108.6
N1—C3—H3B	108.9	H6A—C6—H6B	107.6
P1—C3—H3B	108.9

O1—P1—C3—N1	−40.2 (3)	O2—P2—C6—N2	49.4 (3)
C2—P1—C3—N1	−163.7 (2)	C4—P2—C6—N2	−75.2 (3)
C1—P1—C3—N1	82.7 (3)	C5—P2—C6—N2	172.3 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H11···N2ⁱ	0.86 (3)	1.95 (3)	2.805 (4)	173 (3)
N1—H12···O1ⁱⁱ	0.86 (3)	1.96 (3)	2.824 (3)	177 (4)
N1—H13···O2	0.91 (3)	1.81 (3)	2.716 (4)	172 (4)
N2—H21···O1	0.82 (3)	2.17 (3)	2.965 (4)	163 (4)
N2—H22···I1	0.83 (3)	3.21 (3)	3.948 (3)	150 (4)

Symmetry codes: (i) x, y, z−1; (ii) −x+1/2, y, z−1/2.

Experimental details

Crystal data
Chemical formula	C₃H₁₁NOP⁺·I⁻·C₃H₁₀NOP
M_r	342.09
Crystal system, space group	Orthorhombic, Pca2₁
Temperature (K)	100
a, b, c (Å)	17.7791 (3), 11.1766 (2), 6.91805 (12)
V (Å³)	1374.69 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.54
Crystal size (mm)	0.36 × 0.19 × 0.10

Data collection
Diffractometer	Oxford Diffraction Xcalibur Eos diffractometer
Absorption correction	Analytical [CrysAlis PRO (Oxford Diffraction, 2009), based on expressions derived by Clark & Reid (1995)]
T_min, T_max	0.538, 0.808
No. of measured, independent and observed [I > 2σ(I)] reflections	10904, 3062, 2972
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.016, 0.033, 1.05
No. of reflections	3062
No. of parameters	145
No. of restraints	6
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.28
Absolute structure	Refined as an inversion twin.
Absolute structure parameter	0.173 (17)

Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL2013 (Sheldrick, 2008), DIAMOND (Brandenburg, 2011), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H11···N2ⁱ	0.86 (3)	1.95 (3)	2.805 (4)	173 (3)
N1—H12···O1ⁱⁱ	0.86 (3)	1.96 (3)	2.824 (3)	177 (4)
N1—H13···O2	0.91 (3)	1.81 (3)	2.716 (4)	172 (4)
N2—H21···O1	0.82 (3)	2.17 (3)	2.965 (4)	163 (4)
N2—H22···I1	0.83 (3)	3.21 (3)	3.948 (3)	150 (4)

Symmetry codes: (i) x, y, z−1; (ii) −x+1/2, y, z−1/2.

Acknowledgements

I would like to thank V. Breuers for valuable suggestions. Furthermore, I acknowledge the support for the publication fee by the Deutsche Forschungsgemeinschaft (DFG) and the open access publication fund of the Heinrich-Heine-Universität Düsseldorf.

References

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ISSN: 2056-9890

Volume 69| Part 8| August 2013| Pages o1253-o1254

doi:10.1107/S1600536813019004

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

(Di­methyl­phosphor­yl)methanaminium iodide–(di­methyl­phosphor­yl)methan­amine (1/1)

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(Dimethylphosphoryl)methanaminium iodide–(dimethylphosphoryl)methanamine (1/1)